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Hm. Maybe I'm just a big ironic jerk, then. I always think of some schmoe with a beetling unibrow saying "A classy dame like that you gotta wine and dine before she puts out" (which I suppose is an old style of speech anyway, debarring 'classy' from the list on principle).

I guess if classy is used as a substitute for classist, then it could have a negative connotation. Otherwise, it is my experience that classy, while possibly going out of style as an adjective, is good! Other oldies, but goodies:The cat's meowCreme de la cremeA#1TopsBitchin'Far out....

I have no idea what this conversation's about, but I have been watching it with interest. Maybe I'm not plugged in to culture sufficiently, but in my small circle there is no stigma attached to the word classy at all. Perhaps it's because our class system in the United States is rather more invisible than that in Britain, etc. (though still exists, even though we boast that we don't have one). I would say that it's slightly old-fashioned in the sense that I don't think younger people use it at all—but there are times when no other word will do. I've never actually heard that its origins came from any kind of class system, though that stands to reason.

I used it a few months ago describing a public figure, and I meant it in a complimentary way.

Edit: The OED lists its first usage as 1891:1891 S. J. DUNCAN Amer. Girl in London 228 Why didn't one of you go? Not classy enough, eh? 1892 Temple Bar Nov. 393 Her successor is the ‘smart’ young married woman,..who is chic and ‘classy’. 1899 E. PHILLPOTTS Human Boy 174 He said a man who sold pills and toothbrushes..could not be considered a classy chemist. 1903 ‘MARJORIBANKS’ Fluff-Hunters 94 Was she classy, well-turned out, and all that sort of thing? 1929 Daily Express 2 Jan. 4/2 An assemblage as sophisticated and classy as ever gathered under one roof.

As the OED also defines "class" as separate from "the masses," one wonders why the opposite adjective to classy is not massy. ... I may start using it. :)

duly humbled. I had thought it'd have been born in a context which has no class at all (there was still a smidgen in the 50s).

now, has the meaning changed since the origin of the word? at this point (according to my understanding of the word), nobody can say "classy" without declaring their trashiness; it's the herald of bad taste.

And as I grew up in the UK in the '80s it was (still is) a very common word to signify stylishness - one might speak of a "classy" football player, motor car, restaurant. But it definitely goes back much further than that; in fact it feels slightly old-fashioned now.

Classy, in the sense of "stylish" has been around in American English at least since the 1940s. The book British and American English since 1900 by Eric Partridge and John Williams Clark, published in 1951, notes: "British swanky more or less equals American classy" (and that was all I was shown in the snippet view of Google Book Search). But there are lots of examples.